4-Cyanophenol → HCID 4294756, compound

HRID 1290799Notes

Reaction equation

HRID 1290799 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].Br[CH:13]([C:15]1[N:20]2[N:21]=[CH:22][N:23]=[C:19]2[N:18]=[CH:17][CH:16]=1)[CH3:14]>COCCOC>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH:13]([C:15]2[N:20]3[N:21]=[CH:22][N:23]=[C:19]3[N:18]=[CH:17][CH:16]=2)[CH3:14])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 130194-CyanophenolHCID 24758Sodium hydrideHCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

Product 1

HCID 4294756HCID 4294756, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 4-cyanophenol (1.19 g) in dry 1,2-dimethoxyethane was added slowly to a stirred suspension of sodium hydride (0.48 g) in dry 1,2-dimethoxyethane (35 ml). The mixture was stirred for 30 minutes, then a solution of 7-(1-bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine (2.27 g, prepared in a similar manner to that described in Example 6 below) in dry 1,2-dimethoxyethane (85 ml) was added dropwise. The reaction mixture was stirred overnight at room temperature. The sodium bromide was removed from the mixture by filtration. The solvent was evaporated from the mixture and the residue was dissolved in dichloromethane and washed with 200 ml of a 5% aqueous solution of sodium hydroxide followed by water. The organic layer was dried over magnesium sulphate. Evaporation of the solvent afforded a crude product which was purified by column chromatography on silica gel using as eluent a mixture of ethyl acetate and petroleum ether (in the ratio 6:4 respectively), followed by recrystallisation from ethyl acetate, to give 7-[1-(4-cyanophenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 1.07 g, (m.p. 163°-164° C.).

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. customThe sodium bromide was removed from the mixture by filtration
  4. customThe solvent was evaporated from the mixture
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed with 200 ml of a 5% aqueous solution of sodium hydroxide
  7. dry with materialThe organic layer was dried over magnesium sulphate
  8. customEvaporation of the solvent
  9. customafforded a crude product which
  10. customwas purified by column chromatography on silica gel using as eluent
  11. additiona mixture of ethyl acetate and petroleum ether (in the ratio 6:4 respectively),
  12. customfollowed by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-9feaabf8b1254725b0415fb75f5bdca2
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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